


What Happens At the Roadhouse...

by rizlowwritessortof



Category: Supernatural
Genre: Early-season Dean, F/M, No Angst, Smut
Language: English
Status: Completed
Published: 2020-03-15
Updated: 2020-03-15
Packaged: 2021-03-12 23:30:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23156296
Author URL: https://archiveofourown.org/users/rizlowwritessortof/pseuds/rizlowwritessortof
Summary: Bailey’s just looking for a couple days post-hunt R&R at Harvelle’s - and then he shows up. Cocky bastard.
Relationships: Dean Winchester/Original Female Character(s)
Comments: 1
Kudos: 13





	What Happens At the Roadhouse...

_Harvelle’s Roadhouse, 2006_

Bailey squinted as she entered the bar, her eyes slow to adjust from the bright sun to the dim, dusty light inside. It was sparsely populated, as usual, and she headed for her favorite bar stool. She flung her leather jacket over the chair behind her and took a seat. After a hunt, this was her favorite place to unwind, spend a couple of days with Ellen and Jo, help work the bar, just kick back.

Ellen came out of the kitchen, a twelve-pack in each hand, stepping behind the bar to set them down before she acknowledged her latest customer. A welcoming smile lit her face as she saw Bailey, and she reached into the cooler for a cold one. “Bailey. Good to see you, sweetie. Usual?”

“Yeah, thanks, Ellen. Nice to be back.” She accepted the freshly-opened brew from Ellen and took a swig, then set it down, sighing happily. “Ice cold, just what I needed. How are things?”

“Oh, you know, same shit, different day. Jo’s been gone for about two months straight, I think she’s avoiding me. But nothing much changes around here, you know.”

“Where’s Ash?”

“In his room. Tied one on last night, I think he’s still sleeping it off.”

Bailey grinned. “Sounds about right. Seen the boys?”

“You mean the Winchester boys? They stop in here and there. Why do you ask?” Ellen winked as she asked the question, and Bailey ducked her head to hide the blush.

“No particular reason, lady, mind your business.”

Ellen laughed, low and throaty. “You know that boy’s gonna break your heart.” She took a towel to a couple of glasses, putting them back on the shelf. “If I was your age, though, I might think it was worth the risk.” She wiggled her eyebrows, and Bailey laughed.

“I’ve missed you, Ellen.”

“Backatcha, girl.”

Before she knew it, it was past midnight, and the weariness was catching up. She booked a room and welcomed a hug from her hostess before heading up the creaking stairs. The rooms and the beds were well-worn but clean, and after a quick shower she crawled between the sheets with a grateful sigh, dropping off as soon as her head hit the pillow.

Sunlight tried to peek through the closed blinds, one shaft of light sneaking its way to the side and hitting Bailey right in the eye. She frowned at it, then rolled to her back and stretched. Probably should get up, anyway, see if Ellen needed any help making breakfast or anything. She rubbed her eyes and got out of bed, making her way down the hall to the bathroom, the wood floor chilly on her bare feet.

She came into the hall, still yawning and half asleep, and walked right into a solid wall of man. His hand shot out, taking her arm to keep her from falling on her ass, and she looked up into the amused green eyes of Dean Winchester. “Bailey! Well, my day just got all kinds of better.” His voice was warm and lazy, with that just-woke-up husky quality to it that made her heart trip up a little.

“Dean. Hi. I, uh, didn’t expect to see you.”

His eyes traveled down her body, and she could almost feel them like a caress on her bare legs. “Yeah, I can see that.” The sexy little smirk that curved those sinful lips made her blush, and she jerked her arm away from his grasp.

“Well, don’t let me hold you up. Gotta get downstairs and help Ellen with breakfast.” She hurried back to her room, trying not to think about the fact that his eyes followed her until her door closed and hid her from his view.

“See you downstairs,” he called out, a teasing note in his voice, and then she heard the bathroom door shut and the shower start.

She leaned against the door for a minute, then shook her head and grabbed her bag to get dressed. Damn it. This was not the way things were supposed to go. _She_ was supposed to gain the advantage, leave _him_ stuttering and flustered. In her imagination, that was how it played out, anyway. But being face-to-face with Dean Winchester sent all those plans right out the window, it wasn’t fair. He wasn’t fair, with his stupid hair, and those stupid lips, and his fucking pretty green eyes with the long, long eyelashes, and that solid, broad chest and tight ass and bowlegs and… “Damn it.”

Ellen watched, arms folded, as Bailey worked furiously to set up the buffet line. “We tryin’ to set a new record?” she asked, and Bailey let out a frustrated sigh.

“Just trying to help. If you want me outta your hair, I can go…”

“Something wrong?”

Bailey sighed, rolling her eyes. “Yes. No. I’m sorry, didn’t mean to bite your head off.”

“You wanna talk about it?”

“Maybe later. Thanks, Ellen.”

Bailey was in the pantry searching for an extra bottle of maple syrup when she heard Dean clear his throat behind her. She closed her eyes for a second, took a deep breath and set her face in a neutral mask before turning to face him. “So you finally made it downstairs. Takes a while to get the makeup just right, doesn’t it?”

He made a face. “Ha-ha-ha. You’re a regular comedian. What are you doing?”

“Getting some syrup for Ellen. If you don’t mind.” She stood there, bottle in hand, and waited for him to move.

“I don’t mind.” He stood there, smiling at her, not moving a muscle until she moved towards him, and then moving only as far as absolutely necessary to allow her to squeeze by.

“You’re such a juvenile,” she whispered angrily, trying to ignore his quiet chuckle. 

He ambled into the bar behind her, nodding as Ellen smiled and called out his name. “Dean! When did you get here?”

“Late last night. Didn’t wanna wake you, so we just kind of helped ourselves to a couple rooms.”

“Where’s Sam?”

“Still sleeping, I guess. He was still working on something with Ash when I went to bed.”

“Well, it’s good to see you. Help yourself to some breakfast.”

“Thanks, Ellen.” He looked right into Bailey’s eyes as he continued. “It all looks really tasty.”

She felt herself blushing and clenched her teeth. “Fucking asshole,” she muttered under her breath, and he grinned.

“Heard that.”

“Meant for you to hear it,” she snarked back, then laughed out loud as Ellen walked by, cuffing Dean on the ear.

“Behave yourself, or I’ll kick your ass.”

He looked at the older woman with a sheepish expression. “Sorry, Ellen.” Bailey sent a sunny, victorious smile his way, then turned and followed Ellen into the kitchen.

Bailey hummed quietly to herself as she washed dishes, elbow-deep in the huge sink. The Sunday buffet didn’t bring in a huge crowd or anything, but the Roadhouse didn’t have amenities like a dishwasher, so it had to be done by hand. She had sent Ellen off, telling her to go relax for a change and let her finish cleaning up. Wasn’t easy to win an argument with her, but she finally gave in and headed to her living quarters, probably to work on books or clean her own space, Bailey guessed.

She had put the last dish in the huge drying rack and was drying her hands when Dean walked into the room. “Great timing, there, Winchester.”

His mouth quirked into a one-sided smile. “I could’ve helped, all you had to do is ask.”

Bailey shrugged, hanging up the dish towel. “I offered, she needs to take a break once in a while.”

“Yeah. Woman works hard, that’s for damn sure.” He wandered around the room, and she caught sight of him gnawing at his lip, clearly wanting to say something and not sure how to begin.

“Dean? Something wrong?”

He sniffed, finally turning to face her, hands in his pockets. “I was just wondering what I did, you know, to piss you off. Seems like you’re mad at me. Is it about Des Moines?”

“Des Moines? Why would I be mad at you for Des Moines?”

He shrugged. “I don’t know. Maybe – did I push you into doing something you didn’t want to? I mean…”

“Dean, all we did was make out in a closet. You didn’t push me into anything – like you could make me do something I didn’t want to, anyway,” she laughed, but she could feel the warmth in her cheeks. Damn it, that happened a lot around him.

“It was just a way to pass the time – a really fun way to pass the time,” Dean grinned back. “I thought maybe you were mad about it, I don’t know.”

“We didn’t even really do anything…”

“Second base,” he teased and she grabbed the damp dish towel and threw it at him.

“Oh, and we’re back in high school again.” He was smiling that kind of shy, but secretly pleased smile, looking down at the floor, and she felt a couple of the butterflies in her belly take off. “You know, you could’ve rounded third.” She couldn’t help giggling at his wide eyes when he raised his head in surprise.

“Oh, yeah? Now you tell me.” He moved closer as she leaned back against the sink. “You know, that pantry is pretty much the same size as the closet we were in. When I found you in there earlier, I just wanted to close the door and…” He leaned in, threading his fingers through her hair and moving it back over her shoulder as he brushed his lips over hers, just a barely-there touch. His green eyes were warm as he looked into hers, his tongue darting out to moisten his lips.

“All right, you two, take it outta my kitchen.” Ellen stood in the doorway, her arms folded and a knowing smile on her face. “Go on, we gotta prepare food in this place.”

“Yes, ma’am,” Dean answered, grinning and reaching for Bailey’s hand. She pushed away from the sink and followed, sending a parting smile over her shoulder at the older woman.

“Damn, those were the days,” Ellen muttered to herself, grabbing the ledger she had come for from the corner table and leaving the room.

Dean almost plowed into Sam, who was on his way down the stairs, as he rushed upwards. “Hi, Sam,” Bailey called out as Dean pulled her by, and Sam sent a laughing “Morning, Bailey” after her, continuing down.

“Where we goin’?” Dean asked, coming to a sudden halt.

Bailey pulled at his hand. “Come on.” She headed for her room, letting him follow her in before she closed the door, and he backed her up against it immediately. After kissing her breathless, he took a step back and held out his hand, but she looked back at him, her smile fading a little. “Y’know, I think maybe I do need to say something. About Des Moines.”

His face fell, and she resisted the urge to laugh. “Okay. Tell me.”

She pushed away from the door, chewing on her lip for a second before she spoke. “Well… after that… I don’t know, it was like we kind of left things – unsettled. At least I did. I really expected you to call or something, try to meet up, finish what we started? I don’t know. It just felt like…” She stared down at the floor. “It felt like it was nothing to you. Like maybe I really was just something you did because you were bored, but you didn’t really give a shit about it. When I didn’t hear from you at all, not a message, nothing… And the thing was, and I shouldn’t even tell you this, but I was wound up for days, I couldn’t stop thinking about it, imagining how the rest could have gone. I felt like you just – threw me away. And when you stopped me this morning in the hall, and you were all flirty and cocky, I don’t know… I just wanted to punch the smirk off your face.”

“_You_ think it was nothing to _me_?” He huffed out a sarcastic little laugh. “I _dreamed_ about you. I thought about you every time I…” He let out a frustrated sigh. “I never called you because – because I felt like an idiot. I figured it was no big deal to _you_. I felt like a loser, made out with a girl for twenty minutes and couldn’t fucking get over it. I figured the best thing for me to do was to let it go instead of mooning over you like some fucking nerd teenager.”

“Yeah? Well, I couldn’t let it go.”

“Well, I couldn’t, either.” They stared at each other for a long, lingering moment, and then Dean moved, fast, pinning her against the door and kissing her, all restraint gone. She wrapped her arms around his neck, the fingers of one hand gliding up through his hair, then gripping hard. He moaned, bucking his hips against her, slipping his hand beneath the hem of her shirt and moving up to squeeze at her breast.

He finally lifted his head, panting, pulling his hand from her shirt and working the buttons free, resisting the urge to just yank her shirt open and send them flying. She swallowed hard as he pushed the cloth down her arms and reached for the clasp of her bra, and she shook the shirt from her arms, letting it drop to the floor. Dean stared down at her, his jaw working, grabbing and kneading at her breasts with both hands as he kissed her again, hungry and demanding.

He moved back suddenly, taking her hand and pulling her along to the foot of the bed. A thick quilt hung over the bed frame, a little lower than waist-high, and he looked at it, then looked at her, questions asked and answered without a word. She stared into his eyes as she unfastened her jeans, shoving them down over her hips along with her panties. His eyes fluttered closed for a split second, and then he bent and helped her step out of her clothing, dropping kisses to her thighs and belly, nuzzling into the crease of her thigh and nipping gently before standing back up and stripping his own shirt off. He reached back for his wallet, pulling out a condom as she unfastened the button of his jeans and he watched her, predatory, as she helped him undress.

“I’m gonna fuck you so good,” he murmured in her ear, sending a shiver through her.

“Promise?” she challenged with a smile, and he let out a soft grunt as she gripped his erection, giving it a squeeze before sending his boxers down to his feet.

He stepped out of his jeans and grabbed her by the shoulders, kissing her hard and quick, then turning her towards the bed. “Bend over there for me, Beautiful, and hang on.”

She gladly did as he asked, gasping a little as his fingers stroked through her folds, rubbing at her clit for a delicious moment before penetrating her with two fingers, burying them to the last knuckle. The position she was in left her on the balls of her feet, almost on tiptoe, and she struggled to push back into him, seeking. “Be patient, baby, I don’t want to hurt you,” he said, his voice rough as he worked her open. “God, you’re so tight, so wet for me, I can’t wait to feel you around me.” She was whimpering, fistfuls of the bedding in her hands, trying not to beg, but he wasn’t making it easy.

Finally he withdrew his fingers, and he moaned as he put them to his lips. She waited impatiently, heard the condom wrapper ripping and his quiet hiss as he sheathed himself. “Dean…” she managed to force out as he traced over her body with his fingertips, caressing her curves and giving her ass a squeeze before gripping one hip and lining himself up with the other hand.

She felt everything inside her go fluid as he slowly pushed inside. It seemed like forever before he was flush against her, invading the deepest part of her with such sweet aching pleasure that it was already overwhelming her senses. He was feeling it, too, groaning and gripping her hips hard, his fingertips digging in almost painfully. “You all right, baby?”

“God, yes.”

“You feel fucking fantastic. Better than any of my dreams. And they were pretty damn good.” He began to rock in and out, gentle and barely moving at first, swearing softly under his breath as her body clutched at at him. “Don’t worry, sweet little pussy, I won’t go far,” he muttered as he pulled back, shuddering when Bailey moaned at the impact of him fully impaling her again.

Her nails were digging into the bedding as she struggled to meet his quickening thrusts, but she had no leverage. Her moans turned into breathless cries as he picked up speed and began to drive into her, holding her hips in place. She bit into the quilt covering the bed beneath her, the repeated impact of their bodies building the tension in her until she let go with a muffled scream, her world shattering around her.

Dean was gritting his teeth, his hips a blur as he chased his orgasm, letting out a feral growl as he came hard, his head spinning a little with the force of it. Bailey was whimpering softly, still shuddering and shivering with aftershocks, her legs hanging limp from the bed rail. Dean resisted collapsing over her, his muscles seizing with one last violent shudder before he took a breath and reluctantly pulled out.

He slipped his arms around Bailey’s body and lifted her upright, then swept her up in his arms and moved around to lie her down in the middle of the bed, disposing of the condom before dropping down beside her. After a couple of minutes, she turned towards him, letting him pull her close as she laid her head on his shoulder. “You did not lie,” she whispered, and he smiled. “I mean, a guy says something like that to a girl, and doesn’t follow through? That would be real disappointing. I am not disappointed. Holy shit, Winchester.”

“Glad you had a good time. I had a _great_ time. Better than I imagined, and I’ve got a hell of an imagination. I imagined some pretty amazing things with you after Des Moines.”

“Oh, yeah?”

“Yeah. Maybe sometime…”

“Definitely.” He felt her smile against his skin, and her lips nibbled at him before she spoke again, softly. “You think they heard us downstairs?”

“Nah.”

“Really?”

“Well, probably not. But if they did – what happens at the Roadhouse _stays_ at the Roadhouse.”

She sighed and snuggled closer. “That’s a relief.”


End file.
